Hydrochloric Acid → 5-phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one

HRID 1679359ノート

反応式

HRID 1679359 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].O[CH2:6][NH:7][C:8](=[O:23])[CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+](C1C=CC=CC=1)([O-])=O.Cl>O>[C:11]1([CH:10]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:6][NH:7][C:8](=[O:23])[CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 6451240Aluminum(III) ChlorideHCID 20362665N-(Hydroxymethyl)-β-phenylbenzenepropanamide

生成物 1

HCID 199031995-phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one収率 34%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

8.7 g. (0.065 moles) of aluminium chloride are added to a solution of 7.7 g. (0.030 moles) of N-hydroxymethyl-3,3-diphenyl-propionamide in 300 ml. of nitrobenzene. The reaction mixture is heated, with stirring, at 100° C. for 6 hours and then cooled and poured into 1 liter water containing 5 ml. of concentrated hydrochloric acid. The nitrobenzene is removed by steam distillation and the residue is extracted with chloroform. The organic phase is dried over anhydrous sodium sulfate and then evaporated to dryness. The residual solid is purified by chromatography on a silica column, using a mixture of benzene and ethanol (85:15 v/v) as eluent, and then recrystallized from 2-propanol. 2.4 g. (34% of theory) of 5-phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one are obtained. M.P. 182°-183° C.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperaturecooled
  3. customThe nitrobenzene is removed by steam distillation
  4. extractionthe residue is extracted with chloroform
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residual solid is purified by chromatography on a silica column
  8. additiona mixture of benzene and ethanol (85:15 v/v) as eluent
  9. customrecrystallized from 2-propanol

出典と根拠

ORDレコード
ord-28b9cf4ca4b74d13a60ea29f22c2ce21
出典データセット
uspto-grants-1978_03
特許番号
US04080449

反応ノート

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